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Video courtesy of Bluehour Labs.
Allegra PusateriAugust 28, 2024
There isn’t another city quite like Chicago, making it easy to plan a trip. Architecture and museums, food and bars, beaches and parks, live events—it’s a diverse city that always has something new to do and see. Chicago is also United’s hometown. Many of us at United are either locals or transplants, like myself, that have spent years exploring the 77 neighborhoods that make up this beautiful lakefront city. Here’s what we recommend to get the most out of Chicago.
Before heading out for the day, drop your bags at your hotel. We recommend using United Hotels to find the perfect one. Then, it’s time to explore downtown (or “The Loop”). How you do this all depends on what interests you.
Museum and culture lovers
If you love art, history, science, animals, space or just a museum in general, there are several museums to choose from, especially in and close to The Loop. If you plan to hit multiple museums, we suggest getting a CITYPASS or seeing which ones have free days while you’re in town.
The Art Institute of Chicago has a collection spanning thousands of years, from the 12th century to the present day. Works by Vincent van Gogh, Georgia O’Keefe and Salvador Dali are favorites of United employees. But it’s the Thorne Miniature Rooms (which are exactly what they sound like) that many of us have been staring at since we were kids.
A little further south, you’ll find several more museums fairly close to each other:
You can venture even further south to Hyde Park for the Griffin Museum of Science and Industry, for interactive science exhibits, model trains and more. Head north to the Chicago History Museum in Old Town to learn more about the history of the city.
Sight seers
If your goal is to see as much of downtown as possible, it can be hard to do everything in a day—but this should help narrow it down:
Foodies
Chicago is a food city. You can find top notch food from all over the world here. While a lot of great food is found in the neighborhoods throughout Chicago, the West Loop has some of downtown’s top restaurants. There’s something for every craving, and Michelin Bib Gourmand restaurants are plentiful:
Looking for a Chicago classic? A little north of The Loop, in River North, is Mr. Beef, where you’ll find both a great beef dip sandwich (in my opinion) and the inspiration for The Bear.
Exploring Chicago’s neighborhoods is the only way to see the real city. But, you can’t see them all in one trip, so here are nine that United employees rave about the most.
North side
In nearly every north side neighborhood, you’ll see brownstone houses and apartment buildings next to Michelin-starred restaurants and world-renowned museums.
Uptown
Uptown is just off the lake and Lakefront Trail. Here you’ll find Montrose Beach, a favorite of locals and less crowded than other beaches in the city. Plus, it’s close to Montrose Point Bird Sanctuary, a 15-acre nature preserve great for birding and hiking.
Asia on Argyle is strip off the Argyle Red Line stop packed with a lot. There’s food from all over Asia, largely Vietnam. A popular spot is Bambu, where the bobaristas whip up fresh dessert drinks and foods. Stay after your meal for shopping, murals and a night market in the summer.
For dinner, I recommend the sambussa sampler and a messob from Demera, an Ethiopian hot spot. For a drink, head to the The Green Mill. While this jazz club is infamous for Al Capone’s favorite booth, it’s also long been the center of Chicago jazz and hosts regular poetry slams.
Lakeview
Lakeview, just south of Uptown, is known for its proximity to the lake, Wrigley Field and Boys Town. If you’re in the area check out a drag show like Drag Brunch at The River.
Movie buffs should go to the Music Box Theatre, which has been around since 1929. They show indie, foreign and cult classic films. And if there’s room in your suitcase for a little bit of shopping, Lakeview is littered with vintage, thrift and consignment shops. Studio 32 is a local favorite.
Hungry? Here’s what we love to eat in Lakeview:
Lincoln Park
Taking the Lakefront Trail south from Lakeview, you’ll hit Lincoln Park next. The trail leads you right inside the free Lincoln Park Zoo (the flamingos and polar bears are both a personal favorite). The Lincoln Park Conservatory is nearby and free as well, though you’ll need to make a reservation before you go.
If you want to stop for a drink and live music, head over to Kingston Mines, one of Chicago’s many blues clubs. Koko Taylor, Eric Clapton and Mick Jagger have all played there. While you’re in Lincoln Park, you must try:
West side
Many west side neighborhoods have a trendy yet relaxed vibe. These neighborhoods move at a slower pace than others, but there’s no shortage of night life, food and shopping.
Logan Square
You can’t get to the west side of Chicago from the Lakefront Trail, but it’s close to the Blue Line. If you’d rather walk or bike, The 606 is an abandoned rail line turned paved trail that runs through Logan Square, Humboldt Park, Wicker Park and Bucktown.
Logan Square has great street art. The murals on Milwaukee Ave are ever-changing and quite literally add color to an already vibrant neighborhood. Just west of Milwaukee, you’ll also find City Lit Books. Their staff picks section is always on the money.
When you’re ready to eat, you have a lot of options:
Wicker Park
Continuing south from Logan Square is Wicker Park, where you’ll find an artsy and bohemian vibe. There are both art galleries and boutiques selling clothes where trendy meets vintage, like Saint Alfred and P45. Myopic Books is a three-story shop with over 80,000 books and regular poetry nights. You could spend an entire afternoon there if you wanted. I have. Plus, there’s the neighborhood’s namesake: Wicker Park with its gardens and fountain.
When your stomach starts growling, you have a lot of options in Wicker Park:
Ukrainian Village
Next stop on the west side of town is Ukrainian Village. This is a more relaxed part of the city, but there’s still a lot to do. The Delta M sells both traditional and modern Ukrainian goods, including jewelry, clothes, paintings and more. The Ukrainian Institute of Modern Art features work by some of Ukraine’s most famous artists, and the Vertical Gallery often features emerging local artists.
There’s a variety of food in Ukrainian village, including:
South side
The south side has defined Chicago’s culture and character for decades.
Chinatown
Heading south from The Loop, Chinatown is just off both the Red Line and Green Line. You can also take the Chicago Water Taxi from downtown. It’s a straight shot west from the Lakefront Trail, if you’re biking or walking.
Chinatown Square is a two-story outdoor mall with all kinds of boutiques and restaurants, including Ichiban Candy and Snacks. If you’re looking for a park you can enjoy with the kids, Ping Tom Memorial Park hosts bamboo gardens and a playground with a trail throughout.
No trip to Chinatown is complete without trying the food. Here are our top picks:
Pilsen
Directly west of Chinatown is the Pilsen neighborhood, filled with Latino culture, music, art, nightlife and more. The murals on 16th street are a must-see. They’re everywhere, on the front of homes, on overpasses, on train platforms—big, beautiful works of street art seamlessly integrated into the neighborhood.
18th street is one of the coolest streets in the city, with dozens of restaurants, museums and art galleries (including the National Museum of Mexican Art), bookstores and bars. Don’t just take our word for it—Timeout named 18th street one of the coolest streets in the world in 2024.
You’ll find something to eat at these 18th street favorites:
Hyde Park
Promontory Point is another popular urban hiking spot, thanks to its proximity to Lake Michigan. If you’re interested in architecture, check out Frank Lloyd Wright’s famous Robie House. Lastly, head to Hyde Park Records for vinyl and CDs from various genres and decades.
If you’re looking for the top eats in Hyde Park, we’ve got you covered:
Chicago locals know, there’s always something going on. Whether it’s festivals, comedy, concerts, theater or games—you’ll find a live event for any interest year-round.
Sports
Chicago has nearly every major sport covered:
Music
Chicago is known for gospel and house music, as well as blues and modern jazz. We celebrate our strong music scene throughout the city at both seasonal and year-round venues.
In the summer, it’s all about outdoor concerts and music:
There’s also smaller music venues if that’s more your vibe. The Vic, Lincoln Hall and Salt Shed are all on the north side of the city and places United employees enjoy.
Theater
Chicago is a big theater town—we have Broadway in Chicago and get previews of pre-Broadway plays and musicals. Shows are constantly on rotation, but some of our favorite theaters and companies include:
Comedy
Whether it’s improv (which was invented at the University of Chicago), stand up or open mic nights, you’ll find a great spot to laugh with your friends, family or partner:
Festivals
Summer in Chicago is all about festivals. Some are in parks downtown, and some block entire neighborhood streets. There’s too many to name them all, but here are a few of our favorites:
Here in the cooler months? No worries.
To us at United, Chicago is more than just a homebase for our operations. It’s our hometown. We’re proud of the history, the culture, the sites, the food— and we’re excited to share it with you. See you soon!
Know before you go
Before diving into how to spend your days, let’s talk about how to get around Chicago: